HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Caribbean Islands

$190+ Cheap flights from Madison (MSN) to Caribbean Islands

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 5/14. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — SJU
May 6 — May 131
Tue 5/6
Tue 5/13
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Madison to Caribbean Islands with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Madison to Caribbean Islands

Keep the following information in mind while searching for Madison to Caribbean Islands flight deals. Data was last updated May 1, 2025.

Round-trip from

$225
(American Airlines)

One-way from

$190
(American Airlines)

Popular in

December

Cheapest in

August

Average price

$596
From Madison Truax Field to Caribbean Islands
Search Deals
One-way flight from Madison Truax Field to Caribbean Islands
Search Deals
Highest demand for flights based on searches. 1% potential increase in price ($6 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($15 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2025
Search Deals

Find flight deals from Madison to Caribbean Islands

Cheapest flights from Madison to Caribbean Islands
Explore the most affordable flight options available from Madison to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 1, 2025.

This American Airlines deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/138:27 pmMSN - SJU
2 stops18h 53mAmerican Airlines
Sat 9/203:55 pmSJU - MSN
1 stop6h 33mAmerican Airlines
Deal found 4/29$225
This United Airlines deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/162:35 pmMSN - SJU
1 stop8h 19mUnited Airlines
Tue 7/293:56 pmSJU - MSN
1 stop7h 37mUnited Airlines
Deal found 4/30$389
This Delta deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/26:45 amMSN - SJU
1 stop7h 27mDelta
Sat 8/94:25 pmSJU - MSN
1 stop8h 02mDelta
Deal found 4/30$405
This American Airlines deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/196:13 amMSN - PUJ
1 stop7h 27mAmerican Airlines
Wed 5/283:16 pmPUJ - MSN
1 stop17h 45mAmerican Airlines
Deal found 4/29$455
This Delta deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/215:45 amMSN - SDQ
1 stop7h 02mDelta
Sun 9/283:12 pmSDQ - MSN
1 stop8h 22mDelta
Deal found 4/29$535
This American Airlines deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/224:33 pmMSN - SDQ
2 stops17h 27mAmerican Airlines
Wed 11/58:55 amSDQ - MSN
2 stops14h 29mAmerican Airlines
Deal found 4/30$539
This American Airlines deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/27:14 amMSN - GCM
1 stop7h 41mAmerican Airlines
Mon 12/82:15 pmGCM - MSN
2 stops9h 39mAmerican Airlines
Deal found 5/1$542
This American Airlines deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/107:17 amMSN - NAS
1 stop5h 08mAmerican Airlines
Sun 9/142:45 pmNAS - MSN
1 stop7h 43mAmerican Airlines
Deal found 4/30$545
This Delta deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/305:45 amMSN - STT
1 stop6h 54mDelta
Sat 10/43:50 pmSTT - MSN
1 stop7h 44mDelta
Deal found 4/30$547
This American Airlines deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/84:29 pmMSN - STT
2 stops19h 31mAmerican Airlines
Sat 11/153:20 pmSTT - MSN
1 stop8h 03mAmerican Airlines
Deal found 4/29$549
This American Airlines deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/26:38 amMSN - MBJ
1 stop7h 17mAmerican Airlines
Mon 12/86:00 pmMBJ - MSN
1 stop17h 21mAmerican Airlines
Deal found 4/29$566
This Delta deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/85:30 amMSN - NAS
1 stop9h 34mDelta
Mon 5/123:20 pmNAS - MSN
1 stop8h 41mDelta
Deal found 4/30$575

Cheapflights Fare Finder

Customize your flight search to find flights from Madison to Caribbean Islands that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated May 1, 2025.
Use the filters below to find and compare flights from Madison to Caribbean Islands that are best for you.

Fly from

Madison

Fly to

Caribbean Islands

Route

Depart

Return

Price

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Sat 9/13

8:27 pm-4:20 pm

2 stops18h 53m

San Juan Luis Munoz Marin Intl

Sat 9/20

3:55 pm-9:28 pm

1 stop6h 33m

$225

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Wed 7/16

2:35 pm-11:54 pm

1 stop8h 19m

San Juan Luis Munoz Marin Intl

Tue 7/29

3:56 pm-10:33 pm

1 stop7h 37m

$389

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Sat 8/2

6:45 am-3:12 pm

1 stop7h 27m

San Juan Luis Munoz Marin Intl

Sat 8/9

4:25 pm-11:27 pm

1 stop8h 02m

$405

MadisonPunta Cana

MSN - PUJ

MSNPUJ

Madison Truax Field

Mon 5/19

6:13 am-2:40 pm

1 stop7h 27m

Punta Cana

Wed 5/28

3:16 pm-8:01 am

1 stop17h 45m

$455

MadisonSanto Domingo

MSN - SDQ

MSNSDQ

Madison Truax Field

Sun 9/21

5:45 am-1:47 pm

1 stop7h 02m

Santo Domingo Las Americas

Sun 9/28

3:12 pm-10:34 pm

1 stop8h 22m

$535

MadisonSanto Domingo

MSN - SDQ

MSNSDQ

Madison Truax Field

Wed 10/22

4:33 pm-11:00 am

2 stops17h 27m

Santo Domingo Las Americas

Wed 11/5

8:55 am-9:24 pm

2 stops14h 29m

$539

MadisonGeorge Town

MSN - GCM

MSNGCM

Madison Truax Field

Mon 6/16

6:40 pm-11:15 am

2 stops16h 35m

George Town Owen Roberts Intl

Sat 6/28

3:05 pm-9:20 am

2 stops18h 15m

$542

MadisonNassau

MSN - NAS

MSNNAS

Madison Truax Field

Wed 9/10

7:17 am-1:25 pm

1 stop5h 08m

Nassau Intl

Sun 9/14

2:45 pm-9:28 pm

1 stop7h 43m

$545

MadisonSaint Thomas Island

MSN - STT

MSNSTT

Madison Truax Field

Tue 9/30

5:45 am-1:39 pm

1 stop6h 54m

Saint Thomas Island Cyril E King

Sat 10/4

3:50 pm-10:34 pm

1 stop7h 44m

$547

MadisonPunta Cana

MSN - PUJ

MSNPUJ

Madison Truax Field

Tue 6/10

7:05 am-3:35 pm

1 stop7h 30m

Punta Cana

Thu 6/19

4:35 pm-10:11 am

2 stops18h 36m

$584

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/30

Showing 1-10 of 25 results
1
2
3

Best time to book a flight from Madison to Caribbean Islands

Have a flexible travel schedule? Discover the best time to fly to Caribbean Islands from Madison with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Madison to Caribbean Islands

What is the cheapest month to book a flight from Madison to Caribbean Islands?

Currently, September is the cheapest month in which you can book a flight from Madison to Caribbean Islands (average of $254). Flying from Madison to Caribbean Islands in December is currently the most expensive (average of $336). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from MSN to EPX?

Find hourly flight availability from Madison to Caribbean Islands. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated May 1, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Madison to Caribbean Islands as you normally would.

Rainfall in Caribbean Islands by month

Plan your trip to Caribbean Islands by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Caribbean Islands ranges from 2.2 - 6.1 inches per month. November is typically the wettest month, when rainfall can reach 6.1 in. February is typically the driest time to visit Caribbean Islands when rainfall is around 2.2 in.

Temperature in Caribbean Islands by month

Plan your trip to Caribbean Islands by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Caribbean Islands, use this chart to help with planning. For those seeking warmer temperatures, June is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 77.0 F).

Reviews of airlines servicing Caribbean Islands

Get insights into the airlines that provide service to Caribbean Islands. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Caribbean Islands. Reviews last updated May 1, 2025.
See what other customers who have flown with Delta, United Airlines and American Airlines from Madison to Caribbean Islands have to say. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,934 reviews

Overall

8.0

Comfort

7.9

Boarding

8.2

Food

7.3

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Delta
8.0
Very good
7,934 reviews
Delta
8.0
Very good
7,934 reviews

Overall

8.0

Comfort

7.9

Boarding

8.2

Food

7.3

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
United Airlines
7.4
Good
8,696 reviews
Delta
8.0
Very good
7,934 reviews

Overall

8.0

Comfort

7.9

Boarding

8.2

Food

7.3

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,934 reviews

Overall

8.0

Comfort

7.9

Boarding

8.2

Food

7.3

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Air Canada
7.0
Good
9,245 reviews
Delta
8.0
Very good
7,934 reviews

Overall

8.0

Comfort

7.9

Boarding

8.2

Food

7.3

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

Related info for your journey

Find useful and relevant information for your journey from Madison to Caribbean Islands. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Madison to Caribbean Islands?

    Madison Truax Field (MSN) is the airport you will fly out of if you book a flight from Madison to Caribbean Islands. It is only a 5.4 mi journey to Truax Field (MSN) from Madison’s city center.

  • What are the most popular routes from Madison to Caribbean Islands?

    While some choose either Madison Truax Field - Nassau Intl or Madison Truax Field - Punta Cana, Madison Truax Field - San Juan Luis Munoz Marin Intl is the most popular route from Madison to Caribbean Islands.

  • Can I find deals for flights from Madison to Caribbean Islands that include hotel bookings?

    Yes. In addition to deals on Madison to Caribbean Islands flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Madison to Caribbean Islands?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Madison to Caribbean Islands.

  • Can I find deals for business class flights from Madison to Caribbean Islands?

    Yes. Cheapflights offers flight deals from Madison to Caribbean Islands by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Madison to Caribbean Islands?

    Currently, September is the cheapest month in which you can book a flight from Madison to Caribbean Islands (average of $254). Flying from Madison to Caribbean Islands in December is currently the most expensive (average of $336). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Madison to Caribbean Islands

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to LaGuardia flights
O'Hare Intl to Dallas/Fort Worth flights
O'Hare Intl to Cancún flights
O'Hare Intl to John F Kennedy Intl flights
O'Hare Intl to Las Vegas flights
O'Hare Intl to Newark flights
O'Hare Intl to Los Angeles flights
O'Hare Intl to Seattle flights
O'Hare Intl to Denver flights
O'Hare Intl to Mexico City flights
O'Hare Intl to Sky Harbor Intl flights
O'Hare Intl to Orlando flights
O'Hare Intl to Miami flights
Minneapolis to Dallas/Fort Worth flights
O'Hare Intl to Boston flights
Minneapolis to Seattle flights
Minneapolis to Las Vegas flights
Minneapolis to Denver flights
O'Hare Intl to Philadelphia flights
Minneapolis to LaGuardia flights
O'Hare Intl to Fort Lauderdale flights
O'Hare Intl to Tampa flights
O'Hare Intl to San Diego flights
O'Hare Intl to San Francisco flights
O'Hare Intl to Honolulu flights
O'Hare Intl to Reagan-National flights
O'Hare Intl to Atlanta flights
Minneapolis to John F Kennedy Intl flights
O'Hare Intl to George Bush Intcntl flights
O'Hare Intl to Baltimore flights
O'Hare Intl to Hobby flights
O'Hare Intl to Nashville flights
O'Hare Intl to New Orleans flights
Minneapolis to Newark flights
O'Hare Intl to Vancouver Intl flights
Minneapolis to Sky Harbor Intl flights
O'Hare Intl to Cozumel flights
O'Hare Intl to Austin flights
O'Hare Intl to Santa Ana flights
Minneapolis to Midway flights
O'Hare Intl to Charlotte flights
Minneapolis to Boston flights
Milwaukee to Denver flights
O'Hare Intl to Salt Lake City flights
Minneapolis to Miami flights
O'Hare Intl to Charleston flights
Milwaukee to Seattle flights
Minneapolis to Los Angeles flights
Minneapolis to Orlando flights
Minneapolis to O'Hare Intl flights

Top 3 airlines flying from Madison to Caribbean Islands

Discover the top 3 airlines that operate flights from Madison to Caribbean Islands. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated May 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$264Average$691FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$330Average$638FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$331Average$681FlexibilityNo cancel feeOn-time69%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.